A New Chapter of Legacy: Planning Across Generations for the Whitmans

Current State of Finances

Richard Whitman is in his early 60s, officially retired after the recent sale of his privately held company. The liquidity event pushed his net worth to over $57 million—most of it now held in cash and real estate. He and his wife have adult children in their 30s and several young grandchildren. With work behind him, Richard is turning his attention toward what comes next—not just for himself, but for his entire family.

Despite his wealth, his current portfolio is relatively simple. He’s been paying for traditional AUM services but recently realized that complexity doesn’t always require a high fee. He reached out to us for a second opinion—recognizing that while his portfolio isn’t complicated, his goals are. He’s looking for a true financial partner to help him think strategically about legacy, gifting, and the long-term financial well-being of his children and grandchildren.

The Whitmans already gift generously each year and want to increase those amounts. But Richard is thoughtful about the potential ripple effects. His children are in very different financial situations, and he wants to make sure the assets he passes along are received wisely—invested for the future, not unintentionally eroding over time. He also wants to equip his children with the financial clarity and structures they need to make smart decisions with the wealth they’re inheriting.

At the heart of this transition is a desire for simplicity, family alignment, and a multigenerational tax strategy that protects—not just his estate—but the ongoing financial strength of the people he loves most.

Financial Advisor Insights: What are we thinking about?

Educating Across Generations

One of Richard’s top priorities is helping his children develop their own financial plans—not just handing them wealth, but preparing them to manage it. We support this by offering individual planning relationships with each adult child, so they have their own advisors, not just inherited expectations. This allows us to tailor advice to each person’s financial reality, from those building careers to those already financially independent.

It also gives Richard peace of mind that his gifts are being used intentionally, whether that means investing for the long term, saving for education, or simply understanding the tax consequences of receiving large assets.

Strategic Gifting and Estate Planning

We’re helping the Whitmans evaluate a wide range of gifting options—from annual exclusion gifts and 529 contributions to more advanced strategies like irrevocable trusts, intentionally defective grantor trusts (IDGTs), and discounted entity transfers. Because the children have differing income levels and financial maturity, we vary both the type and timing of gifts—some receive investment accounts, others are supported through education or housing-related strategies.

The goal is to maximize the tax efficiency of the estate across multiple generations—not just to minimize Richard’s estate tax exposure, but to create enduring structures that avoid avoidable tax friction for the family long after he’s gone.

Real Estate and the Family Legacy

The Whitmans own a beloved vacation home that has served as a central gathering place for years. Richard wants the property to remain in the family, but he’s mindful of the logistical and emotional strain that shared ownership can bring. We’re helping him think through governance structures, ownership transitions, and funding strategies (like establishing a trust or LLC to manage expenses and responsibilities) so that the property stays a source of connection—not conflict.

We also guide them through decisions around other real estate holdings, helping evaluate whether to retain, gift, or sell each property in light of family use, tax impact, and maintenance burdens.

Simplifying a High Net Worth Life

Despite his wealth, Richard’s goal isn’t more complexity—it’s clarity. With the business behind him, he wants fewer moving parts, better reporting, and a clear roadmap for his family. We’re helping him unwind unnecessary account structures, review overlapping services, and replace expensive AUM-based management with a transparent, flat-fee planning relationship.

The goal is a more streamlined financial life—one that reflects not just his current balance sheet, but his desire to empower the next generation with confidence, values, and a foundation they can build on.